CA2218724C - Metabolites de saponines du ginseng produits par les bacteries intestinales chez l'homme, et leur application a la preparation d'un medicament anticancereux - Google Patents
Metabolites de saponines du ginseng produits par les bacteries intestinales chez l'homme, et leur application a la preparation d'un medicament anticancereux Download PDFInfo
- Publication number
- CA2218724C CA2218724C CA002218724A CA2218724A CA2218724C CA 2218724 C CA2218724 C CA 2218724C CA 002218724 A CA002218724 A CA 002218724A CA 2218724 A CA2218724 A CA 2218724A CA 2218724 C CA2218724 C CA 2218724C
- Authority
- CA
- Canada
- Prior art keywords
- compound
- pharmaceutical composition
- protopanaxadiol
- group
- glucopyranosyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
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- 150000007949 saponins Chemical class 0.000 title abstract description 36
- 235000008434 ginseng Nutrition 0.000 title abstract description 34
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- 239000002207 metabolite Substances 0.000 title abstract description 29
- 241000208340 Araliaceae Species 0.000 title abstract description 27
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 title abstract description 27
- 235000003140 Panax quinquefolius Nutrition 0.000 title abstract description 27
- 235000017709 saponins Nutrition 0.000 title description 36
- 241000894006 Bacteria Species 0.000 title description 14
- 238000002360 preparation method Methods 0.000 title description 10
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- CJFGBCWGOQRURQ-JFJIKBJRSA-N ginsenoside Mc Chemical compound C([C@H]1O[C@H]([C@@H]([C@@H](O)[C@@H]1O)O)O[C@@](C)(CCC=C(C)C)[C@@H]1[C@@H]2[C@@]([C@@]3(CC[C@H]4C(C)(C)[C@@H](O)CC[C@]4(C)[C@H]3C[C@H]2O)C)(C)CC1)O[C@@H]1O[C@@H](CO)[C@H](O)[C@H]1O CJFGBCWGOQRURQ-JFJIKBJRSA-N 0.000 claims abstract description 16
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- 229920001223 polyethylene glycol Polymers 0.000 description 1
- GRLPQNLYRHEGIJ-UHFFFAOYSA-J potassium aluminium sulfate Chemical compound [Al+3].[K+].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O GRLPQNLYRHEGIJ-UHFFFAOYSA-J 0.000 description 1
- 229940088417 precipitated calcium carbonate Drugs 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 208000016691 refractory malignant neoplasm Diseases 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- NWMIYTWHUDFRPL-UHFFFAOYSA-N sapogenin Natural products COC(=O)C1(CO)C(O)CCC2(C)C1CCC3(C)C2CC=C4C5C(C)(O)C(C)CCC5(CCC34C)C(=O)O NWMIYTWHUDFRPL-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- FIAFUQMPZJWCLV-UHFFFAOYSA-N suramin Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=C2C(NC(=O)C3=CC=C(C(=C3)NC(=O)C=3C=C(NC(=O)NC=4C=C(C=CC=4)C(=O)NC=4C(=CC=C(C=4)C(=O)NC=4C5=C(C=C(C=C5C(=CC=4)S(O)(=O)=O)S(O)(=O)=O)S(O)(=O)=O)C)C=CC=3)C)=CC=C(S(O)(=O)=O)C2=C1 FIAFUQMPZJWCLV-UHFFFAOYSA-N 0.000 description 1
- 229960005314 suramin Drugs 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 235000019605 sweet taste sensations Nutrition 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J17/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J17/005—Glycosides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Ginsenoside Mc répondant à la formule (I), métabolite de la saponine du ginseng produit par la flore intestinale, et agent anticancéreux le renfermant à titre d'ingrédient actif. Outre un nouveau composé, l'agent anticancéreux est constitué d'un ingrédient actif choisi parmi le composé K, le composé Y ou le 20(S)-protopanaxatriol, et les métabolites de la saponine du ginseng produits par la flore intestinale, en association avec un ou plusieurs excipients pharmaceutiquement acceptables. Ledit agent est un nouveau type d'agent anticancéreux car il présente une activité immunostimulante et une activité d'inhibition de la vascularisation des tumeurs et de l'extravasation des cellules cancéreuses.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1019960004217A KR0164266B1 (ko) | 1996-02-22 | 1996-02-22 | 인삼사포닌 장내세균 대사물 및 이를 유효성분으로하는 제암제제 |
| KR1996/4217 | 1996-02-22 | ||
| PCT/KR1996/000281 WO1997031013A1 (fr) | 1996-02-22 | 1996-12-31 | Metabolites de saponines du ginseng produits par les bacteries intestinales chez l'homme, et leur application a la preparation d'un medicament anticancereux |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2218724A1 CA2218724A1 (fr) | 1997-08-28 |
| CA2218724C true CA2218724C (fr) | 2001-11-06 |
Family
ID=19451583
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002218724A Expired - Lifetime CA2218724C (fr) | 1996-02-22 | 1996-12-31 | Metabolites de saponines du ginseng produits par les bacteries intestinales chez l'homme, et leur application a la preparation d'un medicament anticancereux |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US5919770A (fr) |
| KR (1) | KR0164266B1 (fr) |
| CN (1) | CN1182433A (fr) |
| CA (1) | CA2218724C (fr) |
| DE (1) | DE19681353B4 (fr) |
| WO (1) | WO1997031013A1 (fr) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL139307A0 (en) * | 1998-05-19 | 2001-11-25 | Res Dev Foundation | Triterpene compositions and methods for use thereof |
| US20060148732A1 (en) * | 2000-11-17 | 2006-07-06 | Gutterman Jordan U | Inhibition of NF-kappaB by triterpene compositions |
| US6888014B2 (en) | 2001-07-24 | 2005-05-03 | Panagin Pharmaceuticals Inc. | Dammarane sapogenins, their use as anti-cancer agents, and a process for producing same |
| US6949523B2 (en) | 2001-07-24 | 2005-09-27 | Panagin Pharmaceuticals, Inc. | Aglycon dammarane sapogenins, their use as anti-cancer agents, and a process for producing same |
| CN1336232A (zh) * | 2001-09-03 | 2002-02-20 | 李永忠 | 一种纯生物增寿制品 |
| US20030092638A1 (en) * | 2001-09-21 | 2003-05-15 | Dong Huang | Protopanaxadiol and protopanaxatriol and their use as anti-cancer agents |
| KR100465977B1 (ko) * | 2002-01-05 | 2005-01-13 | 주식회사 태평양 | 나노유화기술에 의한 화합물 ｋ를 함유하는 미세 유화 입자 및 이를 사용한 피부 외용제 조성물 |
| KR100835864B1 (ko) * | 2002-05-27 | 2008-06-09 | (주)아모레퍼시픽 | 인삼사포닌 대사 산물을 유효 성분으로 한 미세 유화 입자 및 그 제조방법, 이를 함유한 피부 노화방지용 화장료 조성물 |
| JP4549625B2 (ja) * | 2002-01-05 | 2010-09-22 | 株式會社アモーレパシフィック | 人参サポニン代謝産物を有効成分とする微細乳化粒子及びその製造方法、並びにこれを含有する皮膚老化防止用の化粧料組成物 |
| AU2003202159A1 (en) * | 2002-04-08 | 2003-10-27 | Ginseng Science Inc. | Extract of processed panax genus plant, the preparation method thereof, and compositions containing the same |
| WO2003086439A1 (fr) * | 2002-04-08 | 2003-10-23 | Ginseng Science Inc. | Nouvelle utilisation de l'extrait traite provenant du genre panax et compose de saponine isole a partir de ladite plante |
| CN1508146A (zh) * | 2002-12-13 | 2004-06-30 | 中国科学院大连化学物理研究所 | 一种新型抗肿瘤人参皂苷 |
| AU2003287833A1 (en) * | 2002-12-19 | 2004-07-14 | Panagin Pharmaceuticals Inc. | Use of aglycon protopanaxatriol in cancer therapy |
| KR100485326B1 (ko) * | 2002-12-26 | 2005-04-27 | 주식회사 태평양 | 진세노사이드 화합물 ｋ로 이루어진 히알루론산 생성촉진제 |
| KR100456089B1 (ko) * | 2004-07-15 | 2004-11-09 | 박용진 | 항암 활성을 갖는 산삼 추출정제액을 정제하는 방법 및이를 함유하는 조성물 |
| KR100654172B1 (ko) * | 2005-05-27 | 2006-12-06 | 주식회사 비티진 | 효소반응에 의한 진세노사이드 Ｍｃ 및 진세노사이드Ｍｃ-1의 제조방법 |
| CN101511369B (zh) * | 2006-08-03 | 2012-06-06 | 肿瘤学研究国际有限公司 | 用于抑制血管发生的方法及组合物 |
| US20120263806A1 (en) * | 2007-05-16 | 2012-10-18 | Miller Sandra | Uses of North American Ginseng Fractions for Treating Leukemia |
| US20120322752A1 (en) | 2009-12-08 | 2012-12-20 | Sung Kyun Lee | SOLID DISPERSIONS CONTAINING 20-O-beta-D-GLUCOPYRANOSYL-20(S)-PROTOPANAXADIOL |
| KR102048709B1 (ko) * | 2013-04-24 | 2019-11-27 | (주)아모레퍼시픽 | 진세노사이드 Mc를 함유하는 피부 외용제 조성물 |
| KR102020754B1 (ko) * | 2013-05-03 | 2019-09-11 | (주)아모레퍼시픽 | 진세노사이드 y를 함유하는 피부 외용제 조성물 |
| US10456436B2 (en) * | 2013-11-04 | 2019-10-29 | Wen Luan Wendy Hsiao | Use of herbal saponins to regulate gut microflora |
| US20150126463A1 (en) * | 2013-11-04 | 2015-05-07 | Hong Kong Baptist University | Use of herbal saponins to regulate gut microflora |
| CN107735080B (zh) * | 2015-07-03 | 2020-10-23 | 浙江海正药业股份有限公司 | 一种人参皂苷c-k口服固体制剂及其制备方法 |
| WO2020032448A1 (fr) * | 2018-08-06 | 2020-02-13 | 고려대학교 산학협력단 | Composition comprenant le ginsénoside mc ou mc1 pour prévenir ou traiter des maladies métaboliques |
| CN111053782B (zh) * | 2018-10-17 | 2024-07-05 | 株式会社爱茉莉太平洋 | 包含人参皂苷的组合物 |
| CN115068490A (zh) * | 2022-06-23 | 2022-09-20 | 四川大学 | 人参皂苷ck在制备脓肿分枝杆菌或/和结核分枝杆菌的抑菌剂中的应用 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5857399A (ja) * | 1981-10-01 | 1983-04-05 | Osaka Chem Lab | ニンジンサポニン、その分離法及び製造法並びに用途 |
| JPS6428759A (en) * | 1987-07-24 | 1989-01-31 | Hitachi Ltd | Memory protecting system |
-
1996
- 1996-02-22 KR KR1019960004217A patent/KR0164266B1/ko not_active Expired - Lifetime
- 1996-12-31 US US08/945,422 patent/US5919770A/en not_active Expired - Lifetime
- 1996-12-31 DE DE19681353T patent/DE19681353B4/de not_active Expired - Lifetime
- 1996-12-31 CA CA002218724A patent/CA2218724C/fr not_active Expired - Lifetime
- 1996-12-31 CN CN96193431A patent/CN1182433A/zh active Pending
- 1996-12-31 WO PCT/KR1996/000281 patent/WO1997031013A1/fr not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| DE19681353B4 (de) | 2004-09-30 |
| KR0164266B1 (ko) | 1999-01-15 |
| CA2218724A1 (fr) | 1997-08-28 |
| CN1182433A (zh) | 1998-05-20 |
| DE19681353T1 (de) | 1998-04-16 |
| KR970061909A (ko) | 1997-09-12 |
| US5919770A (en) | 1999-07-06 |
| WO1997031013A1 (fr) | 1997-08-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20170103 |